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Reproterol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Reproterol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Inhalation (MDI),IV
ATC code
Legal status
Legal status
Identifiers
  • (RS)-7-(3-{[2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]amino}propyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.053.579Edit this at Wikidata
Chemical and physical data
FormulaC18H23N5O5
Molar mass389.412 g·mol−1
3D model (JSmol)
  • CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCCNCC(C3=CC(=CC(=C3)O)O)O
  • InChI=1S/C18H23N5O5/c1-21-16-15(17(27)22(2)18(21)28)23(10-20-16)5-3-4-19-9-14(26)11-6-12(24)8-13(25)7-11/h6-8,10,14,19,24-26H,3-5,9H2,1-2H3 ☒N
  • Key:WVLAAKXASPCBGT-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Reproterol is a short-acting[1]β2 adrenoreceptor agonist used in the treatment ofasthma.[2]

It was patented in 1965 and came into medical use in 1977.[3]

Stereochemistry

[edit]

Reproterol contains a stereocenter and ischiral. There are thus twoenantiomers, the (R)-form and the (S)-form. The commercial preparations contain the drug as aracemate, an equal mixture of the two enantiomers.[4]

Enantiomers of reproterol

(R)-Reproterol
CAS number: 210710-33-1

(S)-Reproterol
CAS number: 210710-34-2

References

[edit]
  1. ^Küpper T, Goebbels K, Kennes LN, Netzer NC (December 2012). "Cromoglycate, reproterol, or both--what's best for exercise-induced asthma?".Sleep & Breathing = Schlaf & Atmung.16 (4):1229–35.doi:10.1007/s11325-011-0638-2.PMID 22198635.S2CID 10032756.
  2. ^Virchow JC (1999). "Reproterol: beta-2-agonist, theophylline, or both?".Respiration; International Review of Thoracic Diseases.66 (3):210–1.doi:10.1159/000029379.PMID 10364735.S2CID 203732706.
  3. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 54X.ISBN 9783527607495.
  4. ^Rote Liste 2017 – Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte). Vol. 57. Frankfurt/Main: Rote Liste Service GmbH. 2017. p. 196.ISBN 978-3-946057-10-9.
Adrenergics,inhalants
Short-acting β2 agonists
Long-acting β2 agonists
Ultra-long-acting β2 agonists
Other
Glucocorticoids
Anticholinergics/
muscarinic antagonist
Mast cell stabilizers
Xanthines
Eicosanoid inhibition
Leukotriene antagonists
Arachidonate 5-lipoxygenase inhibitors
Thromboxane receptor antagonists
Non-xanthinePDE4 inhibitors
Others/unknown
Combination products
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists


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